| Modification of 1-substituents in the 2-azabicyclo[2.1.1]hexane ring system; approaches to potential nicotinic acetylcholine receptor ligands from 2,4-methanoproline derivatives. | |
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MedLine Citation:
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PMID: 14629156 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Successful nucleophilic substitution at a methylene attached to the bridgehead (1-) position of the 2-azabicyclo[2.1.1]hexane ring system opens the way to construction of novel derivatives having a wider range of functional groups attached to the 1-position via a methylene "spacer" (including the beta-amino acid homologue of 2,4-methanoproline) and provides access to epibatidine analogues containing heterocyclic substituents and also to further homologation at the 1-position. Displacements with loss of a nucleofuge (e.g., loss of mesylate anion from the 1-mesyloxymethyl derivative) require thermal activation but proceed without the rearrangement initially anticipated in such a strained bicyclic ring system. A novel tricyclic carbamate intermediate 17 has been isolated; nucleophilic attack on 17 leads directly to the isolation of N-deprotected substitution products (with concomitant decarboxylation). |
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Authors:
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John R Malpass; Anup B Patel; John W Davies; Sarah Y Fulford |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 68 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2003 Nov |
Date Detail:
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Created Date: 2003-11-21 Completed Date: 2004-03-24 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 9348-55 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Leicester, Leicester LE1 7RH, United Kingdom. jrm@le.ac.uk |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Aza Compounds
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chemical synthesis*,
chemistry Bicyclo Compounds, Heterocyclic / chemical synthesis*, chemistry Ligands Models, Chemical Molecular Structure Nicotinic Agonists / chemical synthesis*, chemistry Proline / analogs & derivatives*, chemistry* Stereoisomerism Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/2,4-methanoproline; 0/Aza Compounds; 0/Bicyclo Compounds, Heterocyclic; 0/Ligands; 0/Nicotinic Agonists; 147-85-3/Proline |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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